Where did it begin? Was it Newsnight, back in 2019? “Going to Pizza Express in Woking is an unusual thing for me to do”? “I didn’t sweat at the time”? Or can we actually date all the trouble, all the entitlement, all the grandiose self-importance, to the fact that an RAF flypast greeted his birth?

HRH Prince Andrew Albert Christian Edward, born at Buckingham Palace, had a reputation by the time he could walk. As a toddler he would kick the dogs and taunt the staff. As a five-year-old he was thrown in a dung heap by grooms at the Royal Mews in Windsor, sick of him taunting the horses with a stick. As a teenager he acquired the nickname Randy Andy, and as a young man his behavior was so atrocious that a footman punched him in the face. Queen Elizabeth refused his subsequent offer to resign on the grounds that her son had obviously deserved it. Sixty-six years to the day since that flypast, Andrew Mountbatten-Windsor is spending his birthday in police custody. It seems unlikely that anyone bought him a cake.

“Atrocious”: Andrew as a page boy at Westminster Abbey in 1966.

While Charles, as heir, always lived in a gilded cage, Andrew’s gilded existence knew no bars. Indulged by his mother, he spent his childhood annoying almost everyone. Even she was irritated by his habit of climbing onto the roof of Buckingham Palace to tinker with the TV aerial so she couldn’t watch the racing. His idea of fun was to give the Queen Mother a whoopee cushion and sprinkle itching powder on his mother’s bed.

Princess Diana, who grew up with him, remembered him as “very, very noisy and loud. It occurred to me that there was something troubling him. He was happy to sit in front of the television all day watching cartoons. He’s not a goer. And he gets squashed by his family the whole time.” Until Newsnight, when he was 59 years old, his online biography still referred to his sporting prowess as a schoolboy at Gordonstoun. “HRH,” it read, “played rugby, field hockey and captained the 1st XI cricket team.” “He’s not academically bright,” said a friend in 1986, “but he is astute.” A female pupil at the school Andrew briefly attended in Canada described him as “about as subtle as a hand grenade. It’s pathetic.”

For his 21st birthday party Windsor Castle was turned into a tropical paradise, no mean feat for February, and Elton John was hired to perform. Andrew was by then in the Royal Navy, training to be a pilot and exhibiting the ability to irritate he had honed in childhood. One co-worker at a navy air station in Cornwall described him as pig-headed, while another described him as toffee-nosed. “He doesn’t behave like everyone else,” they said. “He wants his own way and when he is around you have to bow and scrape. Even when he drives round the base in his car, you have to salute that. Fancy saluting a flipping car.”

While Charles, as heir, always lived in a gilded cage, Andrew’s gilded existence knew no bars.

He was 22 when he saw active service as a helicopter pilot in the Falklands, possibly the only period of his life on which he can reflect with satisfaction. “Of course I was frightened,” he once said with rare humility. “Everyone was frightened.” By the time he returned, rose between his teeth, the man forever “squashed” by his family was ready to embark on a new phase as its golden boy.

It did not last long. Behind the scenes, footmen were referring to him as Errol Flynn. His first love was Sandi Jones, the pretty blonde daughter of a colonel. “He loves girls,” she told The Sun. “He’s a real character who always tries to make people laugh.” Even his elder brother, Charles, described him, perhaps bitterly, as “the one with the Robert Redford looks”. (He also once said that Andrew’s problem was that he wanted to be him.)

He was the life and soul of the party at stately homes up and down the land, fond of playing “choo-choo train”, in which everyone conga’d round the room shouting “choo choo”.

Barely two years after he came ashore his father was reading him the riot act. On an official tour of California in 1984 he sprayed the press photographers with paint, a “prank” he no doubt thought hilarious. Instead, their expensive equipment was ruined and the work of the trip was overshadowed. Andrew was becoming a braying embarrassment and a furious Prince Philip told him to “pull his finger out and grow up”.

“Pig-headed”: Andrew visiting California in 1984.

But at Ascot that summer, at a lunch hosted by his mother, he threw chocolate profiteroles at a vivacious young redhead called Sarah Ferguson. She evidently enjoyed it and, in an interview to mark their engagement the year after, described falling for his wit, charm and good looks. The bride’s father said Andrew was “an extremely lucky man” and huge crowds stood outside Buckingham Palace on a cloudy July day to watch them kiss.

Like so much else in Andrew’s life, it didn’t last. Four years after they married, Ferguson went on holiday with their two daughters and another man, Steve Wyatt, her financial adviser. Two years after that, the photos came out and the marriage was over. She blamed Charles and Diana for the breakdown of her marriage, her father blamed courtiers, and neither of the divorcing parties looked in the mirror. The marriage had lasted ten years, for four of which they were separated. Fergie complained to a glossy magazine in 1993 that she was sick of being blamed for everything and that “I want out of the whole thing so I can get on with my life”.

In the event she didn’t get out and she didn’t move on. Instead the divorced couple ended up holding court for decades at Royal Lodge in Windsor. She described herself as one half of the happiest divorced couple in the world and described Andrew as “the best man in the world”.

He was also once again putting the royal family in a bind. His naval career was coming to an end and his usefulness as a royal was limited. Sent to Lockerbie in the wake of the Pan Am disaster, he told residents the Americans had it much worse and that it had only been a matter of time before a plane fell out of the sky.

“Pompous prick”: Andrew and his parents, Queen Elizabeth and Prince Philip, on board the H.M.S. Invincible.

He also had no discernible source of income. The wheeze of making him special representative for international trade and investment must have seemed like a brilliant one: send him off to appear patriotic and useful somewhere else. “Prince Andrew,” the Palace said, “is keen to bang the drum for British exports.” Alas, he was similarly inclined to play golf, embarrass far-flung ambassadors with his boorish behavior and run up enormous bills. Britain’s man in Bahrain, deputy head of mission Simon Wilson, recalled that Andrew traveled with an entourage of equerries, private secretaries, valets and a 6ft ironing board to ensure the perfect pressing of his trousers. He was known throughout the Gulf, Wilson wrote, as HBH: his buffoon highness, a man “who appeared to regard himself as an expert in every matter”. A former ambassador to Italy noted Andrew’s fondness for laughing at his own jokes, and described his diplomatic skills as not always conducive to better relations with the people he was supposed to be schmoozing.

Meanwhile, back in England his collection of 72 teddies, most of them wearing sailor suits, kept the home fires burning. A maid recalled four years ago that she had been responsible for arranging them morning and night, in order of size on the bed and in specific places around the room at night. She received a day’s training for the job and, if she got it wrong, he would shout at her. “His two favorite bears,” she recalled, “sat on two thrones either side of the bed.”

Through it all, he appeared to believe that anyone enforcing the rules must be put in their place. Pulled over for speeding on his way to play golf in 2002 he told the policeman he was in a hurry. He refused to undergo routine security screening at Melbourne airport in 2005 before a flight to New Zealand, prompting one member of the security team to describe him as “a pompous prick. Who does he think he is?”

“A braying embarrassment”: Andrew at St. George’s Chapel, Windsor Castle, in 2024.

He wiped the floor with a policeman who mistook him for an intruder at Buckingham Palace, and caused a diplomatic incident when he criticized George W. Bush’s administration over Iraq. He told Tatler in 2000: “I am a good deal more down to earth than people would expect of a member of the royal family. The ivory tower is not a syndrome from which I suffer.” Meanwhile, his ex-wife traveled the world banging the drum for herself and came home to “sell” access to her ex-husband to the News of the World for more than $750,000.

At every step the royal family must have hoped that Andrew couldn’t sink any lower. He lost the trade envoy job. He lost all his patronages, his HRH, his titles and finally his house. On Thursday he was arrested, and tomorrow? Who knows? If Andrew’s inclined to look for a bright side, he might consider it a blessing that his mother didn’t live to see the day. Realistically, he probably won’t.

Hilary Rose is a longtime columnist and features writer at The Times of London